Preparation of an active intermediate

Abstract

A process for the preparation of an organic reactive intermediate that contains a combination of epoxy groups, hydroxy groups and unsaturated groups wherein the process can be utilized to control the amounts of each of the functional groups in the final product. The reactive intermediates are prepared from natural triglyceride plant and animal oils containing unsaturation.

What is claimed is: 
     
       1. A process for the preparation of organic reactive intermediates that contain unsaturated moieties and moieties selected from the group consisting of:
 i. hydroxyl groups, 
 ii. epoxide groups, and, 
 iii. hydroxyl and epoxide groups, 
 
       said process comprising:
 A. predetermining the concentrations of aqueous hydrogen peroxide and organic acid to be used in the process, said acid selected from the group consisting of: 
 i. acetic acid, 
 ii. peracetic acid, 
 iii. formic acid, and, 
 iv. performic acid; 
 B. combining a predetermined amount of oil selected from the group consisting of: 
 a. natural triglyceride plant oils, and, 
 b. animal oils, and, 
 c. a combination of natural triglyceride oils and animal oils, each a. b. and c. having at least 1% by weight of unsaturation selected from the group consisting of: 
 i. mono-unsaturation, 
 ii. poly-unsaturation, and, 
 iii. combinations of mono and poly unsaturation, based on the weight of the oils, with the predetermined amounts of organic acid and hydrogen peroxide in a reaction vessel to form a mixture; 
 C. heating the mixture to at least 45° C. under an inert atmosphere for a period of time of from thirty minutes to 168 hours, with stirring; 
 D. concentrating and deodorizing the product from C. by sparging using a material selected from the group consisting of 
 i. nitrogen, 
 ii. steam, and, 
 iii. air, 
  at a temperature of 90° to 130° C. to provide a product having an acid number of 2.5 to 10 mg KOH/g. 
 
     
     
       2. A process as claimed in  claim 1  wherein in step D., there is a vacuum applied. 
     
     
       3. A process as claimed in  claim 2  wherein the vacuum is in the range of 5 inches of mercury to 29.5 inches of mercury. 
     
     
       4. A process as claimed in  claim 1  wherein step D., there is no vacuum applied. 
     
     
       5. A process as claimed in  claim 1  wherein the intermediate has an epoxide content of 0.0 to 4.1 weight percent. 
     
     
       6. A process as claimed in  claim 1  wherein the intermediate has an epoxide content of 0.1 to 3.5 weight percent. 
     
     
       7. A process as claimed in  claim 1  wherein the intermediate has an epoxide content of 0.8 to 3.0 weight percent. 
     
     
       8. A process as claimed in  claim 1  wherein the intermediate has an epoxide content of 1.2 to 2.8 weight percent. 
     
     
       9. A process as claimed in  claim 1  wherein in step D. wherein the steam has a pressure of 10 to 50 psig. 
     
     
       10. A process as claimed in  claim 9  wherein the steam has a pressure of 20 to 40 psig. 
     
     
       11. A process as claimed in  claim 9  wherein the steam has a pressure of 25 to 35 psig. 
     
     
       12. The process as claimed in  claim 1 , wherein, in addition, there is a mineral acid present. 
     
     
       13. The process as claimed in  claim 12  wherein the mineral acid is sulfuric acid. 
     
     
       14. The process as claimed in  claim 1 , wherein, the molar ratio of hydrogen peroxide to oil is from about 1/1 to 8/1. 
     
     
       15. The process as claimed in  claim 1  wherein the molar ratio of acid to oil is from about 1/1 to 5/1. 
     
     
       16. A product prepared by the process of  claim 1  wherein the intermediate has 0.1 weight percent water or less, an acid number of 2.5 to 10 mg KOH/g and a hydroxyl number of up to about 230. 
     
     
       17. The process of  claim 1  wherein the hydrogen peroxide is in the range of 25 to 85 percent w/w and the organic acid is in the range of 80 to 100 percent w/w. 
     
     
       18. The process of  claim 1  wherein the acid is acetic acid. 
     
     
       19. The process of  claim 1  wherein the acid is formic acid. 
     
     
       20. A process as claimed in  claim 1  wherein the in intermediate has a hydroxyl number of up to about 230. 
     
     
       21. The process of  claim 1  wherein the addition of oil is followed by the simultaneous addition of acid and hydrogen peroxide. 
     
     
       22. The process of  claim 1  wherein the addition of oil is followed by acid and then hydrogen peroxide. 
     
     
       23. A process for the preparation of organic reactive intermediates that contain unsaturated moieties and moieties selected from the group consisting of:
 i. hydroxyl groups, 
 ii. epoxide groups, and, 
 iii. hydroxyl and epoxide groups, 
 
       said process comprising:
 A. predetermining the concentrations of aqueous hydrogen peroxide and organic acid to be used in the process said organic acid being selected the group consisting of 
 i. acetic acid, and, 
 ii. formic acid; 
 B. combining a predetermined amount of materials selected from the group consisting of 
 i. fatty acid chains cleaved from animal triglyceride backbone, 
 ii. plant triglyceride backbone, 
 iii. methyl esters derived from fatty acid chains cleaved from animal triglyceride backbone, and, 
 iv. methyl esters derived from fatty acid chains cleaved from plant triglyceride backbone, that are by-products of the manufacture of biodiesel, each of i to iv having at least 1 percent of unsaturation selected from the group consisting of: 
 i. mono-unsaturation, 
 ii. poly-unsaturation, and, 
 iii. combinations of mono and poly unsaturation, based on the weight of the oils, with the predetermined amounts of organic acid and hydrogen peroxide in a reaction vessel to form a mixture; 
 C. heating the mixture to at least 45° C. under an inert atmosphere for a period of time of from thirty minutes to 168 hours, with stirring; 
 D. concentrating and deodorizing the product from C. by sparging using a material selected from the group consisting of 
 i. nitrogen, 
 ii. steam, and, 
 iii. air, 
  at a temperature of 90° to 130° C. to provide a product having an acid number up to about 10 mg KOH/g. 
 
     
     
       24. A product prepared by the process of  claim 23  wherein the intermediate has 0.1 weight percent water or less, an acid number of 2.5 to 10 mg KOH/g and a hydroxyl number of up to about 230. 
     
     
       25. The product of  claim 1  wherein the product has a Gardner Color number of 7 or less. 
     
     
       26. The product of  claim 24  wherein the product has a Gardner Color number of 7 or less. 
     
     
       27. The product of  claim 1  wherein the product has an inherent odor score of 7 or higher on the General Motors GME 60276 odor testing procedure. 
     
     
       28. The product of  claim 23  wherein the product has an inherent odor score of 7 or higher on the General Motors GME 60276 odor testing procedure.